This product is soluble in alkaline conditions. Sigma routinely tests solubility at 50 mg/ml in 1 N ammonium hydroxide.
B5386
8-Bromoadenosine 3′,5′-cyclic monophosphate
≥97% (HPLC), powder, protein kinase A activator
Synonym(s):
8-Br-A-3:5-MP, 8-Br-cAMP, 8-Bromo-cAMP
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About This Item
Empirical Formula (Hill Notation):
C10H11BrN5O6P
CAS Number:
Molecular Weight:
408.10
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
245-760-6
MDL number:
Beilstein/REAXYS Number:
591930
Pricing and availability is not currently available.
Product Name
8-Bromoadenosine 3′,5′-cyclic monophosphate, ≥97% (HPLC)
Quality Level
assay
≥97% (HPLC)
form
powder
mp
254 °C (dec.) (lit.)
solubility
aqueous base: soluble, clear
storage temp.
−20°C
SMILES string
Nc1ncnc2n([C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O)c(Br)nc12
InChI
1S/C10H11BrN5O6P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-5(17)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,17H,1H2,(H,18,19)(H2,12,13,14)/t3-,5-,6-,9-/m1/s1
InChI key
DVKQVRZMKBDMDH-UUOKFMHZSA-N
Application
8-Bromoadenosine 3′,5′-cyclic monophosphate has been used:
- to treat H295R cells as positive controls for CYP19 induction
- as a membrane permeable cAMP analog to study its effect on short-circuit current (Isc)
- to investigate its potential as an inducer of differentiation in Wharton′s jelly-derived mesenchymal stem cells (WJ-MSCs)
Biochem/physiol Actions
8-Bromoadenosine 3′,5′-cyclic monophosphate is a cell-permeable cAMP analog having greater resistance to hydrolysis by phosphodiesterases than cAMP. 8-Bromoadenosine 3′,5′-cyclic monophosphate activates protein kinase A, inhibits growth, decreases proliferation, increases differentiation, and induces apoptosis of cultured cells.
Cell-permeable cAMP analog having greater resistance to hydrolysis by phosphodiesterases than cAMP.
8-bromo-adenosine 3′,5′-cyclic monophosphate (8-bromo-cAMP), added to hepatocytes during plating helps to increase the acquisition of beta-adrenoceptors.
Features and Benefits
This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
Other Notes
8-Bromoadenosine 3′,5′-cyclic monophosphate is a membrane-permeable cAMP analog.
Sensitive to light and moisture
Disclaimer
Sensitive to light and moisture.
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This Item | |||
|---|---|---|---|
| form powder | form powder | form solid | form powder |
| assay ≥97% (HPLC) | assay ≥97% (HPLC) | assay >97% (HPLC) | assay ≥98% |
| Quality Level 200 | Quality Level 200 | Quality Level 200 | Quality Level 200 |
| storage temp. −20°C | storage temp. −20°C | storage temp. −20°C | storage temp. −20°C |
| solubility aqueous base: soluble, clear | solubility H2O: 100 mg/mL | solubility water: soluble | solubility water: 100 mg/mL, clear, colorless |
| mp 254 °C (dec.) (lit.) | mp - | mp - | mp - |
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Related Content
8-Bromo-cAMP and 8-CPT-cAMP Increase the Density of beta-Adrenoceptors in Hepatocytes by a Mechanism Not Mimicking the Effect of cAMP
Sandnes D, et al.
Pharmacology & Toxicology, 79(1), 15-22 (1996)
Differentiation of human umbilical cord Wharton?s jelly-derived mesenchymal stem cells into endometrial cells
Shi Q, et al.
Stem Cell Research & Therapy, 8(1), 246-246 (2017)
Dopamine increases Na+ absorption in the Reissner's membrane of the gerbil cochlea
Kim C H, et al.
Auris, Nasus, Larynx, 40(3), 266-272 (2013)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| B5386-5MG | 04061832895789 |
| B5386-25MG | 04061833433799 |
| B5386-100MG | 04061833433782 |
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How can I solubilize 8-Bromoadenosine 3',5'-cyclic monophosphate (Product No. B5386)?
1 answer-
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How does the storage temperature relate to shipping conditions?
1 answer-
The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment.
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What is the Department of Transportation shipping information for this product?
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Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
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What is the difference between Product No. B5386 and Product No. B7880?
1 answer-
Product No. B5386 is the free acid form of the material, while Product No. B7880 is the sodium salt. The sodium salt aids in the water solubility of the compund. The biological function of the compounds, once dissolved, is identical.
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How can I store solutions of 8-Bromoadenosine 3',5'-cyclic monophosphate (Product No. B5386)?
1 answer-
The solution should be stored at -20°C, protected from light and will be stable for up to 6 months.
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